CA2706448C - Solvent systems for pour-on formulations for combating parasites - Google Patents

Solvent systems for pour-on formulations for combating parasites Download PDF

Info

Publication number: CA2706448C
Authority: CA; Canada
Prior art keywords: ether; formulation; glycol; formulations; pour
Prior art date: 2007-11-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

CA2706448A

Other languages

English (en)

French (fr)

Other versions

CA2706448A1 (en

Inventor

Ronald Peter Gogolewski

Douglas Cleverly

Paul Thwaites

Mark David Soll

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Animal Health USA Inc

Original Assignee

Merial Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-11-26

Filing date

2008-11-26

Publication date

2016-08-16

2008-11-26 Application filed by Merial Inc filed Critical Merial Inc

2009-06-04 Publication of CA2706448A1 publication Critical patent/CA2706448A1/en

2016-08-16 Application granted granted Critical

2016-08-16 Publication of CA2706448C publication Critical patent/CA2706448C/en

Status Active legal-status Critical Current

2028-11-26 Anticipated expiration legal-status Critical

Links

239000000203 mixture Substances 0.000 title claims abstract description 188
238000009472 formulation Methods 0.000 title claims abstract description 159
239000004540 pour-on Substances 0.000 title claims abstract description 43
244000045947 parasite Species 0.000 title abstract description 28
239000002904 solvent Substances 0.000 title description 36
QOVTVIYTBRHADL-UHFFFAOYSA-N 4-amino-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C(Cl)=C(Cl)Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O QOVTVIYTBRHADL-UHFFFAOYSA-N 0.000 claims abstract description 61
229960000275 clorsulon Drugs 0.000 claims abstract description 59
241001465754 Metazoa Species 0.000 claims abstract description 47
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 38
239000003623 enhancer Substances 0.000 claims abstract description 28
AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 46
SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 46
229960002418 ivermectin Drugs 0.000 claims description 46
WPNHOHPRXXCPRA-TVXIRPTOSA-N eprinomectin Chemical compound O1[C@@H](C)[C@@H](NC(C)=O)[C@H](OC)C[C@@H]1O[C@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C\C=C/[C@@H]2C)\C)O[C@H]1C WPNHOHPRXXCPRA-TVXIRPTOSA-N 0.000 claims description 44
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 39
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238000011282 treatment Methods 0.000 claims description 23
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 15
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ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 10
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230000000699 topical effect Effects 0.000 claims description 10
229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 9
QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 8
OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 claims description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 6
NFIHXTUNNGIYRF-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCCC NFIHXTUNNGIYRF-UHFFFAOYSA-N 0.000 claims description 5
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 5
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
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GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 claims description 2
UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 claims description 2
CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 claims description 2
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IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
BILPUZXRUDPOOF-UHFFFAOYSA-N hexadecanoic acid octadecyl ester Natural products CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC BILPUZXRUDPOOF-UHFFFAOYSA-N 0.000 claims description 2
229940105132 myristate Drugs 0.000 claims description 2
NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 claims description 2
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
229960005323 phenoxyethanol Drugs 0.000 claims description 2
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 abstract description 39
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239000003096 antiparasitic agent Substances 0.000 abstract description 12
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230000000507 anthelmentic effect Effects 0.000 abstract description 8
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239000000921 anthelmintic agent Substances 0.000 abstract description 6
241000282849 Ruminantia Species 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 description 35
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
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239000005660 Abamectin Substances 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 16
239000007788 liquid Substances 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
241000238876 Acari Species 0.000 description 13
241000242711 Fasciola hepatica Species 0.000 description 13
235000014113 dietary fatty acids Nutrition 0.000 description 13
239000000194 fatty acid Substances 0.000 description 13
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230000001965 increasing effect Effects 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
230000015556 catabolic process Effects 0.000 description 12
238000006731 degradation reaction Methods 0.000 description 12
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 12
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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239000000243 solution Substances 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
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241000255925 Diptera Species 0.000 description 8
239000005894 Emamectin Substances 0.000 description 8
GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 8
150000004665 fatty acids Chemical class 0.000 description 8
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RFKSRZIDTYVHLY-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxymethoxy)propane-1,2-diol Chemical compound OCC(O)COCOCC(O)CO RFKSRZIDTYVHLY-UHFFFAOYSA-N 0.000 description 7
IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 7
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Classifications

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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A—HUMAN NECESSITIES
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- A—HUMAN NECESSITIES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P33/14—Ectoparasiticides, e.g. scabicides
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Organic Chemistry (AREA)
Dermatology (AREA)
Molecular Biology (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Tropical Medicine & Parasitology (AREA)
Inorganic Chemistry (AREA)
Toxicology (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA2706448A 2007-11-26 2008-11-26 Solvent systems for pour-on formulations for combating parasites Active CA2706448C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US99020507P	2007-11-26	2007-11-26
US60/990,205		2007-11-26
PCT/US2008/084884 WO2009070687A1 (en)	2007-11-26	2008-11-26	Solvent systems for pour-on formulations for combating parasites

Publications (2)

Publication Number	Publication Date
CA2706448A1 CA2706448A1 (en)	2009-06-04
CA2706448C true CA2706448C (en)	2016-08-16

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ID=40678982

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2706448A Active CA2706448C (en)	2007-11-26	2008-11-26	Solvent systems for pour-on formulations for combating parasites

Country Status (14)

Country	Link
US (1)	US8097266B2 (ja)
EP (1)	EP2222168B1 (ja)
JP (1)	JP5513403B2 (ja)
CN (1)	CN101909450B (ja)
AU (1)	AU2008329706B2 (ja)
BR (1)	BRPI0819849B8 (ja)
CA (1)	CA2706448C (ja)
DK (1)	DK2222168T3 (ja)
ES (1)	ES2693696T3 (ja)
MX (1)	MX2010005685A (ja)
NZ (1)	NZ585499A (ja)
RU (1)	RU2497364C2 (ja)
WO (1)	WO2009070687A1 (ja)
ZA (1)	ZA201003581B (ja)

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2008
- 2008-11-26 US US12/324,066 patent/US8097266B2/en active Active
- 2008-11-26 CA CA2706448A patent/CA2706448C/en active Active
- 2008-11-26 MX MX2010005685A patent/MX2010005685A/es active IP Right Grant
- 2008-11-26 AU AU2008329706A patent/AU2008329706B2/en active Active
- 2008-11-26 DK DK08853615.6T patent/DK2222168T3/en active
- 2008-11-26 CN CN200880123259.8A patent/CN101909450B/zh active Active
- 2008-11-26 NZ NZ585499A patent/NZ585499A/en unknown
- 2008-11-26 JP JP2010536171A patent/JP5513403B2/ja active Active
- 2008-11-26 BR BRPI0819849A patent/BRPI0819849B8/pt active IP Right Grant
- 2008-11-26 RU RU2010126173/10A patent/RU2497364C2/ru active
- 2008-11-26 WO PCT/US2008/084884 patent/WO2009070687A1/en active Application Filing
- 2008-11-26 ES ES08853615.6T patent/ES2693696T3/es active Active
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Also Published As

Publication number	Publication date
BRPI0819849B1 (pt)	2021-01-05
AU2008329706A1 (en)	2009-06-04
JP5513403B2 (ja)	2014-06-04
ZA201003581B (en)	2011-07-27
JP2011504934A (ja)	2011-02-17
NZ585499A (en)	2011-12-22
BRPI0819849A2 (pt)	2016-10-11
CN101909450B (zh)	2014-04-23
EP2222168A1 (en)	2010-09-01
MX2010005685A (es)	2010-09-28
WO2009070687A1 (en)	2009-06-04
AU2008329706B2 (en)	2013-01-10
DK2222168T3 (en)	2018-12-03
RU2497364C2 (ru)	2013-11-10
EP2222168A4 (en)	2011-05-25
CA2706448A1 (en)	2009-06-04
ES2693696T3 (es)	2018-12-13
US20090163575A1 (en)	2009-06-25
BRPI0819849B8 (pt)	2021-05-25
RU2010126173A (ru)	2012-01-10
CN101909450A (zh)	2010-12-08
US8097266B2 (en)	2012-01-17
EP2222168B1 (en)	2018-09-12

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AU2006276997B2 (en)	2012-01-19	Spot-on formulations for combating parasites
AU2018202648B2 (en)	2019-08-01	Topical compositions comprising fipronil and permethrin and methods of use
EP2155755B1 (en)	2016-07-06	Compositions comprising c-13 alkoxyether macrolide compounds and phenylpyrazole compounds
US10307405B2 (en)	2019-06-04	Stable veterinary combination formulations of macrocyclic lactones and imidazothiazoles
AU2013201461B2 (en)	2015-10-29	Solvent systems for pour-on formulations for combating parasites
AU2013204176B2 (en)	2016-06-02	Stable veterinary combination formulations of macrocyclic lactones and imidazothiazoles

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